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Deuters, Barrie Eugene (1964) Studies in the chemistry of borazole systems. Doctoral thesis, Northern Polytechnic.
A literature scan on the structure, preparation and properties of borazole and its derivatives is presented and modem trends in the chemistry of borazole systems, with particular reference to the development of semi-inorganic polymers, are emphasised.
Both o- and p-ethylaniline with boron trichloride afford 1:1 co-ordination complexes which decompose in hot toluene to the corresponding B-trichloroborazole. These were converted to the corresponding N-triethylphenylborazole by reduction with lithium aluminium hydride, or, to the B-trimethyl-N-triethylphenylborazole by reaction with methylmagnesium iodide.
The B-trimethyl-N-triethylphenylborazoles reacted with N-bromosuccinimide resulting in stepwise α -bromination of the ethyl groups. Several ’bromoborazoles’ were thus isolated and characterised by elemental analysis, molecular weight determinations, and nuclear magnetic resonance studies.
B-Trimethyl-N’-p-vinylphenyl-N",N‴-di(α-bromo-p- ethylphenyl)borazole was obtained from B-trimethyl-N-tris (α-bromo-p-ethylphenyl) borazole by dehydro bromination with quinoline.
The interaction of halogenating agents and borazoles containing boron-hydrogen bonds was studied.
Diarylboron halides and arylboron dihalides were prepared by the interaction of boron trichloride and arylmercury halides. The dihalides were mixed with ammonia and methylamine to form, respectively, B-triaryl- borazoles and B-triaryl-N-trimethylborazoles. Vinyl boron dichloride, prepared from tetravinyltin and boron trichloride in a median of petroleum, yielded bis(phenyl- amino)vinylboron when reacted with aniline. Ethylphenylboron dichloride (mixture of o- and p- isomers) with allylamine gave mostly bis(allylamino)-p-ethylphenylboron and some B-tri-p-ethylphenyl-N-triallylborazole.
A series of dialkoxyphosphinylmercuric halides, (Alk0)2P(O)HgX (shown to be dimers by molecular weight determinations in boiling benzene), were prepared in order to explore a new approach to the formation of the boronphosphorus bond.
Condensing B-trichloro-N-triarylborazoles with bis(2- chloroethyl)vinylphosphonate resulted in the elimination of 1:2 dichloroethane and the formation of phosphorus-oxygen-boron linkages. Such linkages were also formed when vinylboron dichloride was condensed with either triethyl phosphate or bis(2-chloroethyl)vinylphosphonate, and when o-ethylphenylboron dichloride was condensed with bis(2-chloroethyl)vinylphosphonate.
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